Trail Running calendar near Guilford 2026-2027

A mountain trail event at Harriman State Park offering a half marathon, a 10K, and a 10K ruck on rugged, technical courses with significant elevation gain and limited crew access at aid stations.

Sleeping Giant Trail Runs at Sleeping Giant State Park in Hamden CT features a 25K loop with 3K+ of vertical and a 50K two-loop option. The course mixes technical singletrack and carriage roads, includes aid stations, and follows a cupless..

A community trail event in Cross River, NY featuring a hilly wooded 5K, a 4K walk through the main trail, and a 200 m kids dash on the contest track. Registration opens 8/24/2026 with limited pre-registration t-shirt incentives.

A 5K trail run and walk at Blydenburgh County Park in Smithtown, NY. The route uses sand, dirt roads, hard packed trails and pavement, supports Last Chance Animal Rescue, and is dog friendly with leash rules.

Trail races of 50K and 17K at Penwood State Park in Bloomfield, CT on April 17, 2027. The loop course features rocky single track on the Metacomet Trail and a nine hour cutoff for the 50K.

A women-centered trail event at Lake Mohegan offering 5K, 10K, and a 4-hour loop on a 3.2 mile trail. The race is open to non-binary runners, follows a cupless aid policy, and includes finisher medals and post-race refreshments.

A spring 10K trail race in Cross River NY on April 25 2027, organized by Leatherman's Loop Races. Entry is by lottery with registration Jan 8 to Jan 11 2027 and the $58 fee includes the park entry.

VCP 50K is a looped trail ultramarathon in Van Cortlandt Park on 01 May 2027. The 50K course starts with a flats lap then ten cross country loops, with stocked aid stations, drop bag access, finisher medal, singlet, meal and beer.

Camp Mountain Laurel offers a family color run plus a 5K trail run and 5K trail walk at Hamden/North Haven YMCA and New Haven YMCA Youth Center on May 8, 2027; registration opens Feb 19 and first 100 pre-registrants receive a giveaway.

A nine hour timed trail ultra on a 2.2 mile loop through Roosevelt Forest in Stratford, CT. Entry is limited to 50 participants and awards go to the runners with the most miles by the race end.

A 5K trail run plus a free kiddie dash at Blydenburgh County Park in Hauppauge, with mixed trail surfaces, on-site parking options, post run refreshments, and proceeds benefiting the Never Stop Running Foundation.

A 5 mile trail race at Muscoot Farm on May 23, 2027 with two kids races on farm trails. The event is organized by Run the Farm Races and is sanctioned by USA Track and Field.

A lake and summit event at Rockland Lake State Park combining a fully accessible 5K paved loop with a rugged 10K trail up Hook Mountain that gains about 1,300 ft and includes steep, rocky sections and one aid station.

The Woodland Ramble Trail Run will take place in Stonington on Saturday 5 June 2027. You can run 5 kilometers.

Trail races at Ward Pound Ridge Reservation on June 6, 2027 include a half marathon and a 10k that pass the summit where the historic fire tower is being reconstructed. Proceeds support Friends of the Fire Tower for accessibility and educat..

An iterated loop endurance race in West Greenwich RI where runners repeat a 3.8 mile loop with 450 ft of climb and must complete each loop within 60 minutes until only one runner remains ready to continue.

A community 5K and 1 mile family walk at Camp Edey in Bayport, NY, featuring a wooded loop course, family activities, participant amenities like finisher medals and photos, and awards across multiple age divisions.